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A new functional bis(m-phenylene)-32-crown-10-based cryptand host for paraquats.

A new functional bis(m-phenylene)-32-crown-10-based cryptand host for paraquats. The pseudorotaxane complex of the new hydroxymethyl cryptand 3 with N,N'-dimethyl-4,4'-bipyridinium bis(hexafluorophosphate), PQ(PF6)2, has an association constant of 2.0(+/-0.3) x 10(4) M(-1). In the crystal structure of 3 x PQ(PF6)2 one of the bonding elements appears to be an aromatic edge-to-face interaction of a paraquat beta-proton with the hydroquinone moiety; this is the first time this interaction has been reported between a cryptand and paraquat. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png The Journal of Organic Chemistry Pubmed

A new functional bis(m-phenylene)-32-crown-10-based cryptand host for paraquats.

Pederson, Adam M-P; Vetor, Ryan C; Rouser, Mason A; Huang, Feihe; Slebodnick, Carla; Schoonover, Daniel V; Gibson, Harry W
The Journal of Organic Chemistry , Volume 73 (14): -5566 – Sep 26, 2008
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A new functional bis(m-phenylene)-32-crown-10-based cryptand host for paraquats.


Abstract

The pseudorotaxane complex of the new hydroxymethyl cryptand 3 with N,N'-dimethyl-4,4'-bipyridinium bis(hexafluorophosphate), PQ(PF6)2, has an association constant of 2.0(+/-0.3) x 10(4) M(-1). In the crystal structure of 3 x PQ(PF6)2 one of the bonding elements appears to be an aromatic edge-to-face interaction of a paraquat beta-proton with the hydroquinone moiety; this is the first time this interaction has been reported between a cryptand and paraquat.

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ISSN
0022-3263
DOI
10.1021/jo8006368
pmid
18549272

Abstract

The pseudorotaxane complex of the new hydroxymethyl cryptand 3 with N,N'-dimethyl-4,4'-bipyridinium bis(hexafluorophosphate), PQ(PF6)2, has an association constant of 2.0(+/-0.3) x 10(4) M(-1). In the crystal structure of 3 x PQ(PF6)2 one of the bonding elements appears to be an aromatic edge-to-face interaction of a paraquat beta-proton with the hydroquinone moiety; this is the first time this interaction has been reported between a cryptand and paraquat.

Journal

The Journal of Organic Chemistry – Pubmed

Published: Sep 26, 2008

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